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After Jessie calls off her third engagement, she swears off serious relationships until she finds the one. That is, until charming but chronically single Aiden comes along. But unbeknownst to Jessie, Aiden has bet his friends that he can convince a woman to marry him by Christmas, which is only four weeks away.
San Francisco. Its four weeks before Christmas. Jessie Patterston, who operates an interior decorating business with her sister and roommate Vivian Patterston out of their apartment, has just broken up with her latest boyfriend, Mike. As he - after Owen and Trent - is the third fiancé with who she has ultimately had permanent cold feet, Jessie believes she is not destined to be married and as such has sworn off men and serious commitments. Aiden MacTiernan, a personal investment advisor, is a love em and leave em kind of guy. Matt Harper, Aidens friend and business associate, says women can smell the non-commitment off of Aiden. As Aiden dismisses this assertion about him, Matt bets Aiden that he cannot get a woman to say yes to his marriage proposal by Christmas. Aiden accepts the bet on the caveat that he gets to pick the target. Meeting at an art function of one of Matt and Aidens clients, Matt encourages Aiden to go after Jessie as Matt knows Jessies new vow of non-commitment having just been turned down by her. Not knowing this piece of information, Aiden, just thinking that shes cute, does choose Jessie as his target. Although Jessie believes Aidens request for her business card is just a pickup line, Vivian offers it to him as a client is a client for their struggling business. As Jessie and Aiden begin to spend time together in she redecorating his condo, they begin truly to fall for each other. There are several obstacles to a Jessie and Aiden happily ever after: Mike is still around and will do anything to show up Aiden in front of Jessie; despite their attraction to each other, Jessie and Aiden consider the other damaged goods - Aiden who had an unhappy childhood coming from a broken home - and may not be willing to take a long term chance on the other; they may not be willing to take a chance on themselves to change what has been their own unsuccessful histories in this department; and the bet coming to light to Jessie which could permanently taint her view of Aiden.
Arielle Kebbel
Jessie Patterston
Andrew W. Walker
Aiden MacTiernan
Kimberley Sustad
Vivian Patterson
Sage Brocklebank
Mike
Karen Kruper
Susan Patterston
Eric Keenleyside
Hank Patterston
Peter Benson
Matt Harper
Michael St. John Smith
Reverend Macey
Chris Cochrane
Charlie
Jordana Largy
Marcie
Kyle Cassie
Owen
Catherine Lough Haggquist
Rhonda
Julian Bailey
Oliver
Matt Bellefleur
Trent
Chad Krowchuk
Stu
Chelsey Reist
Patty
Janet Gigliotti
Caroller #1
Christopher Donald King
Caroller #2
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